N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

Base Information

Chemical Name:N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester
CAS No.:742102-98-3
Molecular Formula:C₄₃H₅₅N₃O₈S₂
Molecular Weight:806.057
Hs Code.:

N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

Synonyms:N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

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Chemical Property of N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

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Technology Process of N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

There total 11 articles about N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 229473-27-2
2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose

: 742102-98-3
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

2: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

3: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

4: 98 percent / HOBt; DiPEA; BOP / dimethylformamide

5: iPrSiH; TFA / CH₂Cl₂

6: 263 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-3-yl ester

: 742102-98-3
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 4.16 g / NaOMe / methanol

2: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

3: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

4: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

5: 98 percent / HOBt; DiPEA; BOP / dimethylformamide

6: iPrSiH; TFA / CH₂Cl₂

7: 263 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium methylate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-aminomethyl-tetrahydro-pyran-3-yl ester; hydrochloride

: 742102-98-3
N-[(1S)-1-({N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl}aminomethyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂

2: 4.16 g / NaOMe / methanol

3: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

4: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

5: 85 percent / aq. iodobenzene diacetate; TEMPO / CH₂Cl₂

6: 98 percent / HOBt; DiPEA; BOP / dimethylformamide

7: iPrSiH; TFA / CH₂Cl₂

8: 263 mg / DiPEA; HOBt; BOP / dimethylformamide

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium methylate; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; (+)-10-camphorsulfonic acid; 2-propanethiol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jm049927q